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Patented Jan. 11,1924.

UNITED STATES :PATENT OFFICE.

MARTIN FREU'ND, DECEASED,

LATE OF FRANKFORT-ON-THE-MAIN, GERMANY; BY

WALTER FREUND, ADMINISTRATOR, OF FRANKFORT-ON-THE-MAIN, AND EDMUND SPEYER, OF FRANKFORT-ON-THE-MAIN, GERMANY.

PRODUCT OF REDUCTION OF OXYCODEINON AND PROCESS OF PREPARING THE 1T0 Drawing. Original application filed July 15, 1921, Serial No. 485,130. Divided and this application filed March 15, 1922. Serial No. 544,010.

(GRANTED UNDER THE PROVISIONS OF THE ACT OF MARCH 3, 1921, 41 STAT. In, 1313.)

To all whom it may concern:

Be it known that MARTIN FREUND, deceased, formerly a resident of Frankforton-the-Main, for whom the undersigned 5 WALTER F REUND, residing at F rankfort-onthe-Main, Germany, citizen of the German Republic, is acting administrator, and I,

EDMUND SPEYER, a resident of Frankforton-the-Main, Germany, a citizen of the German Republic, have invented certain new and useful Improvements in a Product of Reduction of Oxycodeinon and Processes of Preparing the Same (for which we have made application in Germany April 1&, 1916, Patent No. 296,916 in Austria Dec. 9, 1916,

Patent N 0. 75,740; in Hungary Dec. 9, 1916,

Patent No. 71,587; in

1916, Patent No. 75,110; in Norway Dec. 30,

1919, Patent No. 31,235 5 in Czechoslovakia Feb. 10, 1920, Patent No. 2228; in Denmark Dec. 29, 1919; in Sweden Jan. 20, 1920; in Italy Feb. 23, 1920, and Netherlands Dec. 31, 1919), of which the following is a clear, full, and exact description.

The subject of this invention is dihydro oxycodeinon, an unknown derivative of oxycodeinona product described in the German Letters Patent No. 286431-and the process of preparing the same.

Oxycodeinon, having the formula U H NQ, and a melting point of 275 0., by boiling with a solution of sodium hydrosulphite, is reduced to dihydrooxycodeinon of the formula C H N Dihydrooxycodeinon prepared in'such manner is actually identical with dihydrooxycodeinon as prepared in accordance with the specification of the patent application Serial Number 185130, filed July 15, 1921, from which this 40 application is a divisional application.

The identity is shown by the following facts. Dihydrooxycodeinon prepared in accordance with this application crystallizes from alcohol in long jagged columns melting at 222 C. and yields well crystallized salts. Its hydrochloride C, H ,NO,.HC1 crystallizes from water or diluted alcohol in Switzerland Dec. 7, Af

C. Its free xample: 10 grms. oxycodeinon are heat-.

ed with a solution of 20 grms. sodium hydrosulphite' Na S O water. ter a short time complete solution takes supersaturating with soda or ammonia 6 grams dihydrooxycodeinon. are separated in crystalline form.

Having thus described this invention, we claim as new and desire to secure by Letters Patent:

1. The process of preparing dihydrooxycodeinon, melting at 222 (1., which consists in boiling oxycodeinon together with a solution of sodium hydrosulphite.

2. A new product by heating oxycodeinon together with a solution of sodium hydrosulphite, dihydrooxycodeinon having the formula C H NO which crystallizes from alcohol in long jagged columns, melting at 222 0., and yields well crystallized salts and forms an oxime, the hydrochloride of which is isolated in small sticks decomposing at 275 to 278 C. v

In testimony whereof we have hereunto signed our names in the presence of the two subscribing witnesses.

DR. WALTER FREUND, Acting administrator upon the estate of the deceased inventor, Martin Freand. PRIVATE AGENT DR. EDMUND SPEYER.

itnessesz,

FRITZ MAYER, FRIEDRICH L. HAHN.

of reduction, obtained 2 

